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A Pittsburgh Technology Entrepreneur’s 30-Year Playbook | Building a Software Company That Lasts

Interview by Audrey Russo and Jonathan Kersting

What does it take to build a technology company that lasts nearly 30 years and still feels like day one?

On this episode of TechVibe Radio, Pittsburgh Technology Council’s Jonathan Kersting and CEO Audrey Russo sit down with Lou Camerlengo, co-founder of fivestar*, to unpack a three-decade journey in custom software development, leadership, and purpose-driven entrepreneurship.

From launching fivestar* in 1997 to joining the Revision Collective, Lou shares how building “custom homes” for enterprise clients turned into long-term partnerships spanning 5, 10, even 15+ years. He explains why being “built to evolve” has kept the company relevant through multiple waves of technology change, including today’s AI revolution

You’ll also hear how fivestar* blends profit with purpose, contributing over 500 hours of community service and donating 2% of profits to charitable causes.

If you’re an entrepreneur, founder, or technology leader wondering how to scale without losing your culture, this conversation delivers practical wisdom and positive energy.

Listen in to learn:

  • How to build software partnerships that last decades

  • Why culture and autonomy drive innovation

  • Where AI fits into custom enterprise solutions

  • What “business for good” looks like in action

The Pittsburgh Technology Council produces TechVibe Radio to explore Pittsburgh's Technology and Innovation ecosystem.